- Photoadditions of 1- and 2-Naphthols and Derivatives to Acrylonitrile. Conversion of the Cyclobutane Adducts to Cyanoethylnaphthols
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The photoreactions of 1- and 2-naphthol, their trimethylsilyl (Me3Si) ethers, and 1-methoxynaphthalene with acrylonitrile in a 1:1 isopropyl alcohol-tert-butyl alcohol mixture have been investigated.Irradiation of 2-naphthol and acrylonitrile gives 7-cyano-2,3-benzobicycloocta-2,4-dien-6-ol (3) while 2-naphthol trimethylsilyl ether gives the trimethylsilyl ether of 3.Base treatment of 3 or 3 trimethylsilyl ether gave 1-(2-cyanoethyl)-2-naphthol.Photoaddition of 1-naphthol trimehylsilyl ether and acrylonitrile gives8-cyano-2,3-benzobicycloocta-2,4-dien-1-ol trimethylsilyl ether, which is converted to the parent alcohol (6) by acid or to 2-(2-cyanoethyl)-1-naphthol (7) by base.The latter was also isolated in poor yield from the photolysis of 1-naphthol and acrylonitrile.Photoaddition of 1-methoxynaphthalene and acrylonitrile affords 1-methoxy-8-cyano-2,3-benzobicycloocta-2,4-diene (8) and endo-4-methoxy-7-cyano-2,3-benzobicycloocta-2,4-diene (9), in the ratio 1:1. 2,6-Dimethoxynaphthalene adds to acrylonitrile, giving the 7-cyano-6-methoxy-2,3-(2'-methoxy)benzobicycloocta-2,4-diene (16).These photoadditions are of possible synthetic utility for the ortho cyanoethylation of phenols.
- Akhtar, Ikbal A.,McCullough, John J.
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- Radical scavenging capacity of 2,4-dihydroxy-9-phenyl-1 H -phenalen-1-one: A functional group exclusion approach
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2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elata, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore
- Duque, Luisa,Zapata, Carolina,Rojano, Benjamin,Schneider, Bernd,Otalvaro, Felipe
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p. 3542 - 3545
(2013/08/23)
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- Synthesis of musafluorone: A naphthoxanthenone isolated from Musa acuminata
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5-Methoxy-3H-naphtho[2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium b
- Duque, Luisa,Restrepo, Catalina,Sáez, Jairo,Gil, Jesús,Schneider, Bernd,Otálvaro, Felipe
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p. 4640 - 4643
(2010/09/10)
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